Recently Sold Windham, NY Homes

/77
$930,000 Sold Nov 14, 2025

68 Hilltop Dr, Maplecrest, NY 12454
- 4 Beds
- 4.5 Baths
- 3,500 Sq Ft
- Built 1985
Last Sold Summary
- 7% Below List Price
- $266/SF
- 112 Days On Market
Current Estimated Value $919,161

Last Listing Agent Lisa Jaeger Coldwell Banker Village GreenW

68 Hilltop Dr, Maplecrest, NY 12454
/58
$690,000 Sold Oct 24, 2025

73 Cross Rd, Windham, NY 12496
- 3 Beds
- 2 Baths
- 2,792 Sq Ft
- Built 2005
Last Sold Summary
- $247/SF
- 124 Days On Market
Current Estimated Value $712,220

Last Listing Agent Lisa Jaeger Coldwell Banker Village GreenW

73 Cross Rd, Windham, NY 12496
/54
$1,350,000 Sold Aug 08, 2025

12 Jacob Strasse Rd, Windham, NY 12496
- 6 Beds
- 5.5 Baths
- 5,500 Sq Ft
- Built 1988
Last Sold Summary
- 10% Below List Price
- $245/SF
- 41 Days On Market
Current Estimated Value $1,295,946

Last Listing Agent Catherine Quintard Compass Greater NY, LLC

12 Jacob Strasse Rd, Windham, NY 12496
/39
$314,500 Sold Apr 09, 2025

4 French Park Dr Unit 4B, Windham, NY 12496
- 2 Beds
- 2 Baths
- 1,536 Sq Ft
- Built 1983
Last Sold Summary
- 16% Below List Price
- $205/SF
- 278 Days On Market
Last Listing Agent Sharri Cunningham Bunce Realty

4 French Park Dr Unit 4B, Windham, NY 12496
/2
$960,000 Sold Nov 07, 2025

149 Magda Ln, Windham, NY 12496
- 4 Beds
- 5 Baths
- 2,140 Sq Ft
- Built 1988
Last Sold Summary
- 4% Below List Price
- $449/SF
Current Estimated Value $902,456

Last Listing Agent non-member non member NON MLS OFFICE

149 Magda Ln, Windham, NY 12496
/37
$999,999 Sold Mar 10, 2026

20 Brookhollow Ln, Windham, NY 12496
- 3 Beds
- 3.5 Baths
- 3,284 Sq Ft
- Built 2024
Last Sold Summary
- 15% Below List Price
- $305/SF
- 68 Days On Market
Last Listing Agent Pamela King-Belfor Four Seasons Sotheby's Int.

20 Brookhollow Ln, Windham, NY 12496
/59
$875,000 Sold Jun 20, 2025

216 New York 296, Windham, NY 12496
- 3 Beds
- 2.5 Baths
- 2,342 Sq Ft
- Built 1940
Last Sold Summary
- 27% Below List Price
- $374/SF
- 196 Days On Market
Last Listing Agent Elizabeth 'Beth' Alfeld Keller Williams Realty HV Nort

216 New York 296, Windham, NY 12496
/15
$212,500 Sold Jun 13, 2025

0 Ruland Rd Unit 155000, Windham, NY 12454
- Land
- 10 Acres
- $21,250 per Acre
Last Sold Summary
- 6% Below List Price
- 57 Days On Market
Last Listing Agent Regina Tortorella Coldwell Banker Village Green

0 Ruland Rd Unit 155000, Windham, NY 12454
/39
$340,000 Sold Dec 17, 2025

4 French Park Dr Unit 1 (2a), Windham, NY 12496
- 3 Beds
- 2 Baths
- 1,392 Sq Ft
- Built 1983
Last Sold Summary
- 5% Below List Price
- $244/SF
- 88 Days On Market
Last Listing Agent Carol Shaw Shaw Country Realty, Inc.

4 French Park Dr Unit 1 (2a), Windham, NY 12496
/33
$795,000 Sold Oct 27, 2025

233 Begley Rd, Windham, NY 12496
- 3 Beds
- 2 Baths
- 2,542 Sq Ft
- Built 2001
Last Sold Summary
- $313/SF
- 22 Days On Market
Current Estimated Value $788,432

Last Listing Agent Lubomir Hodan Shaw Country Realty, Inc.

233 Begley Rd, Windham, NY 12496
/44
$1,400,000 Sold Feb 06, 2026

2 the Enclave Unit W10, Windham, NY 12496
- 4 Beds
- 4.5 Baths
- 2,600 Sq Ft
- Built 1999
Last Sold Summary
- 18% Below List Price
- $538/SF
- 117 Days On Market
Last Listing Agent Patricia Charbonneau Brainard Ridge Management

2 the Enclave Unit W10, Windham, NY 12496
/68
$960,000 Sold Nov 07, 2025

149 Magda Ln, Windham, NY 12496
- 4 Beds
- 5 Baths
- 2,140 Sq Ft
- Built 1988
Last Sold Summary
- 18% Below List Price
- $449/SF
- 224 Days On Market
Current Estimated Value $902,456

Last Listing Agent Patricia Charbonneau Brainard Ridge Management

149 Magda Ln, Windham, NY 12496
/54
Sold Apr 07, 2025

11 Whisper Creek Dr Unit 601B, Windham, NY 12496
- 3 Beds
- 3 Baths
- 1,506 Sq Ft
- Built 2019
Last Sold Summary
- 92 Days On Market
Last Listing Agent Regina Tortorella Past Member

11 Whisper Creek Dr Unit 601B, Windham, NY 12496
/85
$1,709,999 Sold Feb 09, 2026

12 Lauren Ln, Windham, NY 12496
- 6 Beds
- 4.5 Baths
- 4,855 Sq Ft
- Built 2012
Last Sold Summary
- 2% Below List Price
- $352/SF
- 97 Days On Market
Current Estimated Value $1,716,058

Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW

12 Lauren Ln, Windham, NY 12496
/40
$2,250,000 Sold May 15, 2025

18 White Way, Windham, NY 12496
- 6 Beds
- 6 Baths
- 4,228 Sq Ft
- Built 2015
Last Sold Summary
- 10% Below List Price
- $532/SF
- 82 Days On Market
Current Estimated Value $2,235,097

Last Listing Agent Carol Shaw Shaw Country Realty, Inc.

18 White Way, Windham, NY 12496
/26
$425,000 Sold Dec 15, 2025

410 Big Hollow Rd, Windham, NY 12496
- 3 Beds
- 2 Baths
- 1,344 Sq Ft
- Built 1970
Last Sold Summary
- $316/SF
- 28 Days On Market
Last Listing Agent Diana Polack Compass Greater NY, LLC

410 Big Hollow Rd, Windham, NY 12496
/9
$440,000 Sold Oct 27, 2025

65 Sundance Dr, Windham, NY 12496
- Land
- 15.36 Acres
- $28,646 per Acre
Last Sold Summary
- 12% Below List Price
- 219 Days On Market
Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW

65 Sundance Dr, Windham, NY 12496
/26
$695,000 Sold May 16, 2025

23 Circle Rd, Windham, NY 12496
- 3 Beds
- 3 Baths
- 2,000 Sq Ft
- Built 2024
Last Sold Summary
- 7% Below List Price
- $348/SF
- 106 Days On Market
Current Estimated Value $672,248

Last Listing Agent Carol Shaw Shaw Country Realty, Inc.

23 Circle Rd, Windham, NY 12496
/29
Sold Apr 24, 2025

25 - 4C Stonewall Ln, Windham, NY 12496
- 4 Beds
- 3.5 Baths
- 2,700 Sq Ft
Last Sold Summary
- 1 Day On Market
Last Listing Agent Pamela King-Belfor Four Seasons Sotheby's Int.

25 - 4C Stonewall Ln, Windham, NY 12496
/6
$120,000 Sold Apr 04, 2025

80 Begley Rd, Windham, NY 12496
- Land
- 3.58 Acres
- $33,520 per Acre
Last Sold Summary
- 4% Below List Price
- 120 Days On Market
Last Listing Agent Regina Tortorella Past Member

80 Begley Rd, Windham, NY 12496
/43
$927,000 Sold Aug 15, 2025

92 Northridge Exd, Windham, NY 12496
- 4 Beds
- 3 Baths
- 3,104 Sq Ft
- Built 2003
Last Sold Summary
- $299/SF
- 30 Days On Market
Last Listing Agent Mark McAlpine Compass Greater New York, LLC

92 Northridge Exd, Windham, NY 12496
/36
$310,000 Sold Feb 11, 2026

73 Windham Ridge Rd Unit 16-H, Windham, NY 12496
- 2 Beds
- 2.5 Baths
- 1,058 Sq Ft
- Built 1986
Last Sold Summary
- 9% Below List Price
- $293/SF
- 161 Days On Market
Current Estimated Value $311,701

Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW

73 Windham Ridge Rd Unit 16-H, Windham, NY 12496
/42
$300,000 Sold Dec 04, 2025

333 Begley Rd, Windham, NY 12496
- 3 Beds
- 2 Baths
- 1,568 Sq Ft
- Built 1998
Last Sold Summary
- 9% Below List Price
- $191/SF
- 26 Days On Market
Last Listing Agent Sharon Knudsen Coldwell Banker Village GreenW

333 Begley Rd, Windham, NY 12496
/31
$550,000 Sold Aug 08, 2025

89 Siam Rd, Windham, NY 12496
- 4 Beds
- 1 Bath
- 2,270 Sq Ft
- Built 1972
Last Sold Summary
- 8% Below List Price
- $242/SF
- 119 Days On Market
Current Estimated Value $548,614

Last Listing Agent Lisa Jaeger Coldwell Banker Village GreenW

89 Siam Rd, Windham, NY 12496
/22
$255,000 Sold Apr 07, 2025

24 Quads Way, Windham, NY 12496
- 2 Beds
- 2 Baths
- 1,008 Sq Ft
- Built 1986
Last Sold Summary
- 5% Below List Price
- $253/SF
- 140 Days On Market
Current Estimated Value $255,739

Last Listing Agent Lacey Sala Keller Williams Realty HV Nort

24 Quads Way, Windham, NY 12496
/19
$485,000 Sold Dec 18, 2025

804 Mitchell Hollow Rd, Windham, NY 12496
- 7 Beds
- 2.5 Baths
- 3,114 Sq Ft
- Built 1852
Last Sold Summary
- 91% Below List Price
- $156/SF
- 55 Days On Market
Current Estimated Value $552,042

Last Listing Agent Chris Tripsas Reliant Property Services

804 Mitchell Hollow Rd, Windham, NY 12496
/14
$1,525,000 Sold Feb 12, 2026

10 Enclave Dr N Unit 106, Windham, NY 12496
- 3 Beds
- 3 Baths
- 1,655 Sq Ft
- Built 2005
Last Sold Summary
- 8% Below List Price
- $921/SF
- 203 Days On Market
Last Listing Agent Irene Pinto Brainard Ridge Management

10 Enclave Dr N Unit 106, Windham, NY 12496
/26
$700,000 Sold Apr 02, 2025

22 Brook Hollow Ln, Windham, NY 12496
- 4 Beds
- 2 Baths
- 2,842 Sq Ft
- Built 2007
Last Sold Summary
- 2% Below List Price
- $246/SF
- 42 Days On Market
Current Estimated Value $710,065

Last Listing Agent Wyatt Dusenbury Corcoran Country Living

22 Brook Hollow Ln, Windham, NY 12496
/74
$1,535,000 Sold Nov 19, 2025

869 County Route 10 Rd, Windham, NY 12496
- 5 Beds
- 4.5 Baths
- 3,812 Sq Ft
- Built 2023
Last Sold Summary
- 1% Below List Price
- $403/SF
- 40 Days On Market
Current Estimated Value $1,490,377

Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW

869 County Route 10 Rd, Windham, NY 12496
/72
$1,311,000 Sold Dec 30, 2025

61 Cambridge Heights Rd, Windham, NY 12496
- 5 Beds
- 3.5 Baths
- 4,214 Sq Ft
- Built 1970
Last Sold Summary
- 9% Above List Price
- $311/SF
- 30 Days On Market
Current Estimated Value $1,097,224

Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW

61 Cambridge Heights Rd, Windham, NY 12496
/30
$1,400,000 Sold Sep 18, 2025

4 The Loop, Windham, NY 12496
- 4 Beds
- 3 Baths
- 2,536 Sq Ft
- Built 1974
Last Sold Summary
- 6% Below List Price
- $552/SF
- 121 Days On Market
Current Estimated Value $1,297,982

Last Listing Agent Patricia Charbonneau Brainard Ridge Management

4 The Loop, Windham, NY 12496
/25
$1,200,000 Sold Apr 30, 2025

5344 Main St, Windham, NY 12496
- 3 Beds
- 3 Baths
- 6,400 Sq Ft
- Built 1975
Last Sold Summary
- 7% Below List Price
- $188/SF
Last Listing Agent Phil Uhrik Past Member

5344 Main St, Windham, NY 12496
/29
$1,675,000 Sold May 12, 2025

21 - 4A Stonewall Ln, Windham, NY 12496
- 5 Beds
- 4.5 Baths
- 3,148 Sq Ft
- Built 2024
Last Sold Summary
- 12% Below List Price
- $532/SF
- 0 Days On Market
Last Listing Agent Pamela King-Belfor Four Seasons Sotheby's Int.

21 - 4A Stonewall Ln, Windham, NY 12496
/42
$655,000 Sold Dec 23, 2025

442 Mitchell Hollow Rd, Windham, NY 12496
- 3 Beds
- 2.5 Baths
- 2,868 Sq Ft
- Built 1969
Last Sold Summary
- 6% Below List Price
- $228/SF
- 146 Days On Market
Current Estimated Value $651,710

Last Listing Agent Mark McAlpine Compass Greater New York, LLC

442 Mitchell Hollow Rd, Windham, NY 12496
/34
$420,000 Sold Jul 14, 2025

296 Mitchell Hollow Rd, Windham, NY 12496
- 3 Beds
- 1 Bath
- 1,486 Sq Ft
- Built 1847
Last Sold Summary
- 4% Below List Price
- $283/SF
- 33 Days On Market
Current Estimated Value $407,496

Last Listing Agent Allison Morelle Coldwell Banker Village GreenK

296 Mitchell Hollow Rd, Windham, NY 12496
/59
$1,392,500 Sold Mar 06, 2026

3 the Enclave, Windham, NY 12496
- 4 Beds
- 4.5 Baths
- 2,893 Sq Ft
- Built 2002
Last Sold Summary
- 13% Below List Price
- $481/SF
- 116 Days On Market
Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW

3 the Enclave, Windham, NY 12496
/30
$397,500 Sold Nov 25, 2025

1020 Maplecrest Rd, Windham, NY 12439
- 4 Beds
- 2 Baths
- 2,267 Sq Ft
- Built 1980
Last Sold Summary
- 1% Below List Price
- $175/SF
- 54 Days On Market
Last Listing Agent Mary Donovan Gallagher & Company

1020 Maplecrest Rd, Windham, NY 12439
/44
$840,000 Sold Jun 20, 2025

429 Mill St, Windham, NY 12496
- 4 Beds
- 3.5 Baths
- 2,294 Sq Ft
- Built 2003
Last Sold Summary
- 1% Below List Price
- $366/SF
- 31 Days On Market
Current Estimated Value $845,897

Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW

429 Mill St, Windham, NY 12496
/52
$685,000 Sold Dec 15, 2025

128 Mount Greenery Rd, Windham, NY 12496
- 4 Beds
- 3 Baths
- 2,759 Sq Ft
- Built 1989
Last Sold Summary
- 6% Below List Price
- $248/SF
- 44 Days On Market
Current Estimated Value $698,493

Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW

128 Mount Greenery Rd, Windham, NY 12496
/54
$398,000 Sold Mar 23, 2026

17 Mitchell Hollow Rd, Windham, NY 12496
- 4 Beds
- 3 Baths
- 1,914 Sq Ft
- Built 1900
Last Sold Summary
- 9% Below List Price
- $208/SF
- 98 Days On Market
Last Listing Agent Sharri Cunningham Bunce Realty

17 Mitchell Hollow Rd, Windham, NY 12496

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